James O'Reilly

Work

  • Jan 2026 - Present
    Zalando
    Senior Software Engineer
    • Migrated Board entities into centralized read-optimized systems and restructured their ERNs in coordination with multiple impacted teams.
    • Authored a technical design document for Boards as a Platform, enabling teams to create custom board styles through dynamic layouts and entity rendering.
  • Aug 2024 - Dec 2025
    Zalando
    Software Engineer
    • Founding engineer on Zalando’s Boards team, building Pinterest-style social features from scratch for millions of customers.
    • Delivered incremental value through controlled rollouts using experiments, feature toggles, and comprehensive monitoring.
    • Helped progress the product from Zalando-curated boards to user-generated boards and AI-powered product recommendations.
    • Worked closely with data scientists to architect and launch Zalando’s first AI-powered product suggestion system.
    • Led technical planning sessions, authored a technical design document, and drove cross-team reviews for architectural alignment.
  • Sep 2022 - Jul 2024
    LearnUpon
    Senior Software Engineer

    LearnUpon is a cloud-based LMS that helps businesses provide continuous employee training. I led development on the company’s first AI integrations.

    AI-powered exam generator

    • Built an OpenAI integration into a Rails application, enabling LMS users to generate exams from course content using natural language.
    • Engineered custom context and prompts, transforming AI responses into dynamic UI elements programmatically.
    • Navigated latency, context guardrailing, and non-deterministic output challenges.
    • Presented findings to the CTO and leadership team, helping secure approval for further AI initiatives.

    AI learning assistant and microservices architecture

    • Architected the backend for an interactive AI chatbot that helped learners reflect on completed courses.
    • Refactored an OpenAI-specific integration into a provider-agnostic messaging library with swappable providers.
    • Built a Golang microservice for asynchronous AI processing, using Kafka between the Rails monolith and the service to improve latency and reliability.
  • Apr 2016 - Dec 2021
    Marino Software
    Senior Software Developer

    Expressway / Bus Eireann - National transport platform

    • Led backend development for the complete relaunch of Ireland’s national coach operator platform.
    • Built a serverless Ruby architecture on AWS Lambda using the SAM framework.
    • Implemented infrastructure as code with CloudFormation for automated deployments.
    • Served as technical lead in client meetings, translating business requirements into scalable delivery plans.

    Permanent TSB - Mobile banking

    • Transitioned into iOS development, rapidly upskilling in Swift and UIKit to deliver critical banking features.
    • Shipped an end-to-end credit card application flow covering multi-step workflows, customer data collection, address verification, and real-time backend validation.
    • Coordinated with Permanent TSB backend teams to support API integration and approval status handling through the verification pipeline.